Mixed Signals
by LadyDivine91
Summary: Kurt and Sebastian made a pact their freshman year that if they haven't had sex by their senior year, they'd have sex with one another. Kurt is still a virgin, but Sebastian has already had sex, so he tells Kurt that makes their arrangement null and void. It's an easy out because he doesn't want to admit just how much in love with Kurt he is. But Kurt doesn't take it. Kurtbastian.
1. Chapter 1

**Best friends Kurt and Sebastian made a pact their freshman year of high school that if they haven't had sex by their senior year, they'd have sex with one another. Kurt is still a virgin, but Sebastian has already had sex - lots of sex - so he tells Kurt that he feels that makes their arrangement null and void.**

 **It's an easy out because he doesn't want to admit just how much in love with Kurt he is, and that having him once, then never again, would break his heart.**

 **But Kurt doesn't take it.**

 _ **A/N: Okay, so I've been writing this one for the better part of two years. I don't know that I'm entirely happy with it, but I feel that it's done. So, here it is. Tell me what you think.**_

"Are you _sure_ you want to do this?" Sebastian asks, his hands tightening around the steering wheel of his Lexus. "I mean, are you really _really_ sure?"

Kurt sighs. When he'd found the nerve to bring the subject up at the first traffic light, Sebastian asked that same question. So far, he's asked it at every light since. And Kurt has said _yes_ every time. But this time around, Sebastian adds, "Why? Have you thought about it? _Really_ thought about it? Because I just … I don't understand."

An emotionally exhausted Kurt gives Sebastian a one shoulder shrug. He thought Sebastian might have a few objections, but honestly, Kurt didn't think it would be _this_ big a headache. "I think … I kind of always knew that my first time would be with you anyway so I might as well, you know, get it out of the way."

Sebastian can't look at his best friend after that. "Gee. Thanks."

"I … I'm sorry. That didn't come out right." Kurt's gaze falls to his hands in his lap, which have been strangling one another since he got in the car. It's a grey day, cloudy overhead, a light rain dotting the windows. It's the first rainy day of spring. Many Dalton students were bummed when it started raining, but Kurt thought that the rain, heralded by a low roar of thunder and flashes of blue lightning in the distance, seemed somewhat romantic.

And that's what he wants for his first time more than anything else.

 _Ambiance_.

"It's alright." Sebastian exhales. "I think I know what you mean."

"Sebastian" - Kurt turns in his seat to face his friend staring intensely out the windshield at the busy intersection - "you're my _best friend_. Aren't you?"

"Yeah," Sebastian says quietly, pulling through the intersection on autopilot when the light turns green. "Yeah, I am."

"And we agreed freshman year that if we hadn't had sex with anyone by the time we were seniors, we'd do it with each other."

"But I've already had sex," Sebastian points out, voice cracking slightly around the word _sex_ because he's not exactly proud of it. Having sex, for him, hadn't been about love. It had barely been about attraction. It was more about curiosity. But once he found someone willing, he became addicted – not just to the act and the pleasure, but to the feeling of power that it gave him. He went from being Sebastian Smythe, snarky asshole, to Sebastian Smythe, sex god, and he liked the way that felt. He liked the way boys in school looked at him because of it. He liked the way the upperclassmen treated him with respect. But there came a time when he realized that he gave away something he didn't know was important to him instead of saving it for someone special.

 _Someone special_ happens to be sitting beside him right now, asking him to make good on a dangerous promise. "So doesn't that make this arrangement null and void?"

"I … I didn't think of it that way," Kurt says, his voice becoming smaller with each word. "It's just that … you've had more opportunities than me. More guys want _you_. I didn't have that. I still don't." He rolls to his right hip and stares out the window. "And it looks like you don't want me either."

"Kurt. It's not … it's not that."

"It's alright," Kurt says, wiping away the fog his breath makes on the glass with the side of his hand. "To be honest, I don't know why I thought you'd agree anyway. That pact we made … it was stupid. I should have known better than to try and hold you to it."

"Kurt, I … dammit!" Sebastian pulls his car out of traffic, over to the nearest curb, and puts it in park with the engine running. "It's not that I don't want you." He reaches for Kurt's shoulder, but his hand remains hovering in the air just above. A second later, he returns it to his lap. Touching Kurt has always been easy – a hand on his shoulder, an arm inside his, their hands linked together. But while sitting in his car having this particular discussion, it seems condescending, much in the same way it feels when your dad claps you on the shoulder like you're bosom buddies right before he tells you you're not old enough to do something you want. "It's that … you're my best friend. When we made that pact, we were kids, not thinking about the consequences of our actions. It seemed like no big thing. But I know what sex between two people can do to a relationship. I don't want to risk losing your friendship over this. It means too much to me."

"It won't ruin it," Kurt says, not able to imagine how in the world it could. Kurt loves Sebastian. He always will. In fact, he can't see this doing anything but bring them closer. Secretly, he hopes it will. And if it doesn't? He'll have had one moment of bliss with him, and he can finally let it go. "I won't let it. I promise."

Sebastian catches Kurt looking at him in the reflection of the window, brow pinched in the middle, blue eyes pleading for him to say _yes_. All Sebastian can think is _this isn't a good idea_ , but he can't bring himself to say it. He doesn't want Kurt to think he's rejecting him for any other reason than he doesn't want to lose him. But if Kurt's promising, and Kurt always keeps his promises …

"Alright," Sebastian says, his defeat palpable – a gargoyle sitting in his chest, weighing him down. "Your place or mine?"

"Yours." Kurt sits up straight, folding his hands in his lap again, bubbling with excitement while, in the driver's seat, Sebastian's stomach rolls itself into a knot, turns to lead, and migrates to his feet.

Sebastian drives extra cautiously on the way to his house. Thank God for the rain giving him an excuse. He can't take the long way or Kurt will know he's stalling, but he wants to give Kurt time to back out. He begs Kurt with significant glances and uncomfortable sighs to change his mind the whole way until they reach the black iron gate of the Smythe estate. Sebastian punches in his code and drives through, praying that Kurt will change his mind, that they'll get to his room and he'll say, "You know what? I'm not ready for this. Can we watch _Moulin Rouge_ instead?" and then that will be the end of that - for today, at least.

But Kurt doesn't.

He practically skips from Sebastian's car to the garage door, then grabs Sebastian's hand and pulls him up the staircase to his room. Once they get there, Kurt falters a step, but only because he's trying to decide between taking off his blazer and tie, or letting Sebastian do it for him, neither of which helps Sebastian, who has pictured undressing Kurt a dozen times, certain it would never happen.

Sebastian paces his room. He has to keep moving or else he might puke. He picks up a lacrosse trophy from his bookcase and moves it to his desk, then he moves it back, switching it out for a picture of him and Kurt taken last summer at Lake Cody. Kurt is wearing a swimsuit in the picture – a pair of unattractively boxy board shorts - but he's also shirtless which, for the moment, adds insult to injury, especially considering the amount of times Sebastian has used that photograph as masturbation fuel. Not in a creepy way. It's not solely about Kurt's body when Sebastian fantasizes about his best friend. It's about the things they have in common, the jokes they share, and the things they do together - the movies they watch, the music they listen to.

It's about how comfortable they are around one another, how fond they are of each other, even if their relationship didn't start off that way.

"So … did you have an idea how you wanted to do this?" Sebastian asks when he can't see a way out of it. He needs to stop thinking of this as a prison sentence. He's not a condemned man.

"What do you mean?" Kurt asks, fingers twisted inside the Windsor knot of his tie, having pulled it loose but not undone.

"Like a fantasy or something?"

Kurt lifts his eyes to the ceiling, smile growing and cheeks pinking as he bites his lower lip. "I've always imagined my first time being on a dewy meadow of lilac with Taylor Lautner."

Sebastian's eyebrows shoot up. He didn't know that. He wouldn't even have guessed that! How is he only hearing this for the first time _now_?

Sebastian isn't Taylor Lautner, but maybe he can swing the dewy meadow of lilac. He glances out the window at the long stretch of grass that extends from his end of the house toward the pool. There's a patch of _something_ purple growing out there. Sebastian can't see it from here, but he knows it's there. And it's been raining, so that might count as 'dewy'. But a fork of lightning flashes that turns the grey sky a blistering white. The rain starts pelting the windows with tremendous force, and Sebastian decides that taking their amorous activities outside isn't the best idea. It would be tragic if Kurt drowned during his first time … or got electrocuted. Explaining that to Kurt's father when he showed up at the hospital would be beyond awkward.

"Uh … I'm not sure I can deliver that, Kurt."

Kurt crosses his arms over his chest and gives himself a hug, lips pulling tight in embarrassment. "Well, what would _you_ do if you actually _wanted_ to have sex with me?"

Sebastian would laugh at that question if he didn't think it would sound cruel - if Kurt didn't look so self-conscious. The truth is Sebastian _has_ a fantasy. _Multiple_ fantasies, some of them so involved there's no way he could execute them without giving himself away. So he decides to keep things simple. As far as Sebastian knows, Kurt has yet to be kissed – not one that Kurt feels counts. There were one or two first kisses with girls when Kurt tried to play it straight, hoping for more of his father's attention.

Sebastian often wondered, if Kurt knew ahead of time that his father had already guessed he was gay, would those kisses have happened?

Either way, he's never been properly kissed by a boy before – anything more than a chaste kiss on the lips.

Sebastian's body shivers with want to give him that.

He takes a steadying breath and thinks, ' _Well, here goes nothing_.'

"Let's start with this."

He puts a hand to Kurt's cheek and leans in, but Kurt jerks away.

"Wait … what are you going to do?"

"I'm going to kiss you, Kurt," Sebastian explains, still leaning in undeterred.

"Oh."

"Don't you _want_ me to kiss you?" His gaze moves between Kurt's lips and his eyes. He chuckles. He can't help it. His best friend is so adorably confused by what he's doing, it's endearing.

But Sebastian doesn't want to see him as adorable. Kurt is _hot_. He's _sexy_. He's desirable, unique, one-of-a-kind.

Unfortunately, he's all of those things with the innocent, wide eyes of a bichon frise.

"Y-yes," Kurt stutters because before his eyes, his best friend changes – his voice becomes sultry, his eyes go dark, the palm caressing his cheek feels hotter. Kurt trembles. This is happening. This is _actually_ happening. He can't _believe_ this is happening.

And it's happening with _Sebastian_.

After this, Kurt should be able to die a happy boy. "Yes. Please, kiss me."

"Alright."

"Wait. Should I … should I count to three?"

"Do you want to?"

"Uh … yes?"

"Then go ahead. Whatever makes you comfortable."

"Okay." Kurt nods, swallows hard. He's excited, and though he looks mildly terrified as well, it makes Sebastian excited. This feels like a dream, one he's had too many times to count. Except it's real. Kurt is here, and this may be the only time Sebastian gets to have him. "One, two …"

Sebastian doesn't let Kurt get to three. He wants to take him by surprise. He wants to make this unforgettable. If he could have his way, Kurt would want him so badly after this one kiss that he'd have no choice but to be _his_ from this day forward.

Friends. That's what Kurt promised – they would remain friends.

Keeping his best friend is the most Sebastian can hope for.

Sebastian wraps his arms around Kurt, sliding his hands up his back till one reaches the base of his head and cradles. Sebastian holds him close, possessively, fitting their lips together as if they had all the time in the world. This is exactly how Kurt dreamed of being kissed, how he dreamed of being held. He thought he'd have to search years, be more experienced, before he found a man who could fulfill his fantasy.

Little did he know that that someone was waiting for him behind Sebastian's bedroom door.

Had he known, would he have come to his best friend sooner?

They part reluctantly with a breath left between them. Kurt seems stunned, unable to move as he comes to terms with the fact that he's just been kissed – a _real_ kiss, the first ever of his life. But something about that kiss gets under Sebastian's skin. It motivates him. He wants this. He's always wanted this. He longs to feel Kurt's body against his, feel his heart beating against his chest as if it were his own. He doesn't want power over Kurt, not like he has with other boys. Quite the opposite. He wants to _give_ himself to Kurt. He wants a first time with Kurt. He wants to make this good for him, for the both of them. He knows he can.

He doesn't want to rush, but he can't wait to get started.

Sebastian kicks off his shoes and pulls off his socks. He tosses off his pants, followed by his shirt, his undershirt, and his briefs, and suddenly, as Kurt watches, it becomes too real. There are things happening, things he's seeing, that he never anticipated, that he wasn't prepared for. The first, and probably the most jarring, is Sebastian naked. _Completely_ naked. And not naked like shower-in-the-locker-room naked (which Kurt never has, but which he's definitely passed by and noticed because _how can you not notice_?), but aroused naked, which is a thousand percent different – Sebastian's heavy breathing, the dark look in his eyes, the rosy flush to his skin, the hair between his legs, and his cock, hard and bobbing, leaking at the tip. Leaking because of the prospect of having sex or because of _him_ , Kurt is reluctant to ask. But these are things that Kurt never included in his fantasies because it never dawned on him to add them.

And he especially never thought he'd see them on Sebastian.

"Are you okay?" Sebastian asks, more worried than flattered by Kurt's drop-jawed expression and held breath.

"Wha-what?" Kurt gives himself a mental shake. "Yeah. I'm great. P-perfect. Fine. Why?"

"Well, you were so gung-ho when we got here, but now you seem stuck on stupid."

Kurt hates that term 'stuck on stupid', but it's the disappointment in Sebastian's voice that brings him out of his stupor. Kurt doesn't know what changed Sebastian's mind, why he's inexplicably so eager, but he's definitely not about to look a gift horse in the mouth.

"I … I just … I guess I didn't realize …"

"Didn't realize what?"

"I didn't realize how …" Kurt has to stop himself from looking Sebastian over from head to toe for the eighth time. He doesn't want to be rude, _but Jesus Christ!_ "… how incredibly handsome you are."

"You're just saying that," Sebastian replies, taking himself by surprise. He has no doubts about his looks. He prides himself on them. He's had other boys call him handsome and more. But hearing it from Kurt, in the heat of this moment, makes it seem truer.

"I'm … I'm not." Kurt shudders as Sebastian reaches out for him, undoing his tie, unbuttoning his shirt. "You … you are. And I …"

"You're handsome, too, you know." Sebastian lines Kurt's lips with kisses as he slips the shirt from his shoulders.

"Not like you," Kurt admits, lifting his chin up as Sebastian moves down his neck. "I'm not as … as athletic … or as dashing …"

"Shhh. Don't …" Sebastian hushes him as he travels down his body. He's used to Kurt's self-deprecating commentary, but he can't listen to it now. Sebastian has seen boys with gorgeous bodies before. But Kurt's is gorgeous in ways that Kurt refuses to see. Sebastian wants to show him that even if other boys at their school are ignorant enough to overlook the wondrous things about him, one person hasn't.

One person hasn't for the past seven years.

Kurt happens to have Sebastian's favorite body type. He doesn't spend hours in the gym like some guys, trying to turn into something he's not. His lean muscles and flat stomach come from _living_ – eating right, dancing, cheerleading, singing. But he's soft in places, too, the way a boy his age should be. He's not trying to grow up too quickly – today's request notwithstanding.

But who is Sebastian to judge? He was a sophomore when he had his v-card punched.

Kurt waited till senior year.

Kurt is tempted to peek down at Sebastian as he makes his way south of the equator, peeling down Kurt's slacks and underwear as he goes, but he's paralyzed. He's not scared. Anxious, but not scared, not anymore. It's easier for him to lose himself this way, separate himself from his apprehensions and simply focus on what his best friend is doing to him. He worries about how he smells or tastes. That's another thing he'd never considered during his fantasies, but it's a very real concern to him at the moment. He does have one thing going for him.

They didn't have P.E. today.

But Sebastian doesn't go that route. He seems married to the task of getting Kurt undressed. Once he pulls down Kurt's briefs, he takes a few moments to appreciate what Kurt has – what no one but his doctor has seen. He kisses down Kurt's shaft, licks a few times around the head, but leaves it at that, and Kurt is relieved. Unpleasant tastes and smells aside, considering how his cock responds to that touch, had Sebastian taken him in his mouth, he'd probably shoot straight down Sebastian's throat in seconds.

Kurt doesn't want this to be over, not when it nearly took an act of Congress to get him here.

Sebastian kisses a trail back up Kurt's body and finds his lips again. Sebastian's amazing mouth occupies Kurt's mind completely, tugging gently at his lips and constantly whispering his name – _"Kurt … oh, Kurt …"_ Strong arms move him to the bed. He registers the sensation of floating until he lands on the mattress, Sebastian's comforter and pillows underneath him.

"How are we doing this?" Sebastian asks, his husky voice in Kurt's ear the thing dreams are made of.

"Wha-what do you mean?"

"I mean - me in you, or you in me?"

"Uh … you in me? I don't think I'm ready for the other way just yet."

"Fair enough."

Sebastian normally doesn't give his lovers a choice. He's not too fond of being entered, though he has been a couple of times. It's nothing more than personal preference. But for Kurt, he'd do it.

He'd do anything for Kurt.

Sebastian continues kissing Kurt, pressing their bodies together, covering Kurt's body with his own so he can be full of him. He raises Kurt's arms above his head and pins them at the wrists, only letting go to reach somewhere out of sight and grab a condom and a bottle of lube. Kurt is curious where he had those stashed since they seemed nearby and at the ready, but he doesn't want to be the one to break their kiss and find out. Sebastian eventually does, turning his face to the side and tearing open the condom packet with one hand and his teeth. Kurt inhales quickly in anticipation, then scrunches his nose.

"What?" Sebastian asks, kneeling to roll the condom down his length. Kurt watches, a little less mystified but eyes still glued to the act.

"I just … I didn't think condoms would smell like that." Kurt takes another sniff, the odor more pungent now that it's unrolled, and giggles. "It's sort of gross."

Sebastian has a remark, but he holds back. This is Kurt's first time, his first firsthand experience with anything sexual really. As far as Sebastian knows, all Kurt knows from (graphic) sex is what he saw in the fourteen-and-a-half seconds of porno he walked in on Sebastian watching one afternoon during Winter Break. Romance is important to Kurt. Condoms aren't romantic. They just aren't. They're utilitarian. But Sebastian has used so many of them, a lot about them has escaped his notice. Kurt is making an observation. Sebastian can't shoot down everything Kurt says.

He gives himself a second to think about. He takes a breath in. His nose scrunches, too.

Kurt is right. They do smell gross.

"Yeah, alright," he concurs. "But they're a necessary evil, so try to overlook it."

Sebastian goes back to kissing Kurt, as Kurt had hoped, but instead of holding his wrists above his head (which Kurt kind of liked), he's toying with the bottle of lube. Amidst Sebastian's intoxicating kisses, Kurt's heart starts to pound. It's a turn on for Sebastian, feeling Kurt's heart drum over his own, but for Kurt, it's more of a cry.

As much as Kurt wants to have sex, this is the part he's looking forward to the least.

There's no amount of bracing in the world that's going to prepare Kurt for this.

Sebastian anticipates resistance. It happens during most first times, even with boys who finger themselves in private. But Kurt's lower half literally turns to stone. Once Sebastian gets past Kurt's pinched cheeks, he finds Kurt's entrance, the muscle squeezed so tight it feels like circling solid rock.

Sebastian tries everything he can think of to get Kurt to relax – kisses to his neck and shoulders, sucking on his nipples, even a few more licks around the head of his cock. But the more he tries to touch his rear, the more he massages and strokes, the tenser Kurt becomes. Sebastian sighs. All of this anxiety, all of this doubt, all of this mental negotiation and gambling, and he's stuck right at the starting gate.

"Kurt, honey, you're gonna have to relax."

"I-I am relaxed," Kurt says, his voice so taut it jumps an octave.

"Well, do you think you could get _more_ relaxed?"

"Like … how much more?"

"Well, at this rate, maybe you should be asleep for your first time."

"Ha-ha. Very funny. Can't you just … shove it in?"

"Yeah, if I wanted to bend my dick in half. Or tear something. I don't want to hurt you, Kurt!"

"I know, I know." Kurt grinds his teeth till his head starts to throb, on the brink of laughing and crying at the same time. He knew that his first time might be problematic and that it could hurt, but he didn't know it would be _this_ difficult. He didn't know that his body would reject Sebastian's attempts at entering it. It's never like this in the movies. He's only seen a handful of NC17 rated rom-coms, but they make it seem like, if you can get your clothes off, everything else just sort of falls into place. "It's just … this is so weird."

"Because … because of _me_?"

"No!" Kurt answers quickly. "No, not because of you! Not at all! It just … it doesn't feel natural. Or particularly sanitary."

"Look …" Sebastian takes a breath, biding his time to think, which is impossible when his body, for one, is ready to go. He should call it quits, convince Kurt that sex – at least, penetrative sex – isn't all it's cracked up to be. He could just blow Kurt. Regardless of what the girls at Crawford Country Day like to tell one another, oral sex is still sex. It's right there in the name. As far as Sebastian is concerned, if he blew Kurt, that would still count as him losing his virginity.

But he knows that's not what Kurt wants.

In the middle of Sebastian struggling with this conundrum, Kurt begins massaging his shoulders, drawing lines between the freckles on his skin with delicate strokes of his fingertips. It feels too good. Kurt's touch is so unpracticed but so familiar. Sebastian doesn't want it to end. But he has to turn Kurt over, get him on his hands and knees if he has any chance of entering him. He'd given it a go with Kurt lying on his back because Sebastian thought that would be more romantic. He could kiss him on the lips, look into his eyes.

If Kurt would agree to make out with him for the next hour or so while Sebastian gave him a hand job, they could still do that. Maybe that would be a decent compromise?

Sebastian watches Kurt's frustrated face morph into a hopeful expression. Kurt deserves more than a compromise. He deserves this, if this is what he wants.

"Concentrate on relaxing," he says, taking Kurt by the shoulders and turning him over. Kurt complies, flipping first on to his stomach, then rising to his hands and knees when Sebastian pulls up on his hips.

"O-okay," Kurt mutters. "I'll … I'll just relax."

"Good. Deep breaths."

"Deep … breaths," Kurt repeats as Sebastian begins to touch him, begins to kiss him, begins to run a slick finger around the entrance of his hole and try over and over to seduce him open.

"Why don't you try and think about someone you want to make love to," Sebastian suggests as he sucks lightly at Kurt's neck. "You said you have a fantasy about Taylor Lautner."

"T-Taylor Lautner's a b-bit out of my league, don't you think?" Kurt asks, his voice unsteady as Sebastian finally manages to slide his index finger inside. He crooks it, then slowly works it in and out, adding another without asking when he knows Kurt is ready. Slowly, patiently, he unlocks places in Kurt's body that Kurt didn't know existed – places of pleasure so extreme they're almost too embarrassing to enjoy.

"No, he's not."

Swirling in a mist of euphoria, Kurt laughs, bitterly considering everything he had to go through to get to this point with his best friend – the boy who was supposed to be a _sure thing_. "You're just saying that."

"No, I'm not," Sebastian whispers into Kurt's neck. "I'm not just saying that. He's _not_ out of your league. No one is. Anyone would be lucky to be with you."

Kurt is tempted to laugh out loud this time, but the sincerity in Sebastian's tone stops him. Right here, right now, Kurt is the _sure thing_. Sebastian doesn't have to flatter him to have sex with him, best friend or not. "R-really?"

"Really, Kurt. Anyone. Now, pick someone and concentrate."

There's a pause, and an emptiness when Sebastian removes his fingers, but that's replaced by an overwhelming fullness when Sebastian starts to enter him, inch by inch in and out, punctuated by the most sinful sounding moans in between.

In his head, Kurt scrolls through a list of the men he's ever found attractive – John Stamos, Ezra Miller, what's his name from that TV show _The Flash_ , the boy who sits in front of him in math class, pre-stepbrother Finn Hudson. Eventually, Kurt settles on the boy whispering in his ear, kissing his shoulder, moaning against his skin. And when Kurt does, he feels himself melt, his overly critical self lifting away.

"Oh God, Kurt … oh God … you feel … so incredible …"

Kurt tries to respond. He opens his mouth, compliment on his tongue. But as Sebastian moves, snapping his hips in a smooth and steady rhythm, those words dissolve. What Sebastian is doing to him feels sublime. _Too_ sublime. And a lump, like coal, forms in his chest, burning in his heart.

Kurt knows that his best friend isn't a virgin. He didn't ask for details, but he knew that Sebastian had been having sex with other boys from Dalton regularly up until a few months ago. It bothered Kurt, but he didn't dwell on it. Or he tried not to. It wasn't a part of _their_ relationship together. Sebastian didn't kiss and tell, so it was easy for Kurt to pretend like Sebastian's sex life was as non-existent as his own.

They aren't two virgins fumbling their way through this act together.

It isn't until Sebastian starts fucking him that Kurt realizes exactly how experienced his best friend is.

"That's it, baby," Sebastian says. "Just relax and let go. I'll make you feel good. I promise."

And Sebastian does. He does things for Kurt he's never done for any other boy. He kisses him gently, explores his body with his hands and his tongue, hugs him, holds him, never more than a few inches apart from him.

He doesn't have sex with Kurt. He _makes love_ to Kurt. And that's a first for Sebastian.

But Kurt doesn't know that. He doesn't know that this time, for Sebastian, is significant.

"God, Kurt," Sebastian moans. "I'm going to cum, I swear …"

"M-me, too," Kurt mumbles, not convinced he is. He feels like it, heat building up inside him the way it has on the rare occasions he's masturbated, but he's not quite there yet. He needs a little something more.

"Are you sure?" Sebastian asks, winding an arm around Kurt's waist and reaching for his cock. The second his fingers wrap around and hold, Kurt gasps. His eyes pop, his jaw drops, and everything comes into focus.

"Oh, God," he squeaks, his mind dropping out of existence. He feels like he's levitating, the only thing keeping him from lifting away into the atmosphere - Sebastian's arm around his waist.

Sebastian starts to stroke. He must feel the waves rolling through Kurt's body because he begins to speed up. He braces himself with one arm against the wall and yet still manages to kiss Kurt tenderly on the back of the neck. The fact that he can do it all at the same time leaves Kurt in awe. But then he remembers – Sebastian can do it because he's had practice. Because he's done this before.

Because Kurt isn't his first, and he probably won't be his last.

And that thought nearly ruins Kurt's orgasm.

As it is, it's stunted compared to what he thought it would be, but it's still better than anything he's ever experienced alone.

Because he's with someone who knows what they're doing.

Because he's with _Sebastian_.

Kurt has always considered himself mature for his age – more mature than his best friend by far. But now, on his hands and knees beneath Sebastian's body, he feels more like a teenager than he has in a long time. As Kurt cums in Sebastian's arms, his head dropping forward with Sebastian's forehead pressed against his neck, Kurt can't help but wonder – was Sebastian's first time like this? Why did he do it? Why would you make yourself this vulnerable to someone? Why would you do this with someone unless you loved them, heart and soul?

Oh God! Did Sebastian love the boy he lost his virginity to? He … he doesn't think so, but he can't be sure. How does Kurt not know for sure?

Shame washes through him as he realizes he doesn't know for one reason and one reason alone.

He's selfish. Sebastian tried to talk to him about it after it happened but, childishly, Kurt stuck his fingers in his ears and started chanting, "Na, na, na, na …" He didn't want to know. He didn't want to imagine his best friend in that position. It was the only real boundary they had in their relationship.

And it was created because Kurt is the worst friend ever.

So much for being the _mature_ one.

Sebastian wraps his arms around Kurt's chest and rests his head against his shoulder.

"Oh, God … oh, Kurt …" he groans, sated.

Relaxed.

 _Satisfied_.

And even though Kurt came, he doesn't feel any of those things.

Kurt stops breathing. He starts hyperventilating. He covers his face with his hands.

 _What has he done?_

He thought he could do this, thought he could remove himself from his deeper feelings about Sebastian, or indulge in them safely, and get this over with, but he was wrong. He was naïve and wrong and now …

"Kurt?" Sebastian's purrs against Kurt's neck stop. "Are you … are you okay?"

"No," Kurt mumbles through his fingers, nails digging into his hairline. _How could he be so stupid?_

"What's wrong?"

Kurt shakes his head. What is he supposed to say? How does he tell his best friend that this wasn't about some dumb pact? That it wasn't really even so much about losing his virginity? That he wanted to have sex with Sebastian because he knew he couldn't have him?

How does he look at Sebastian after today? How does he bear the pain when Sebastian finds a new conquest?

"I'm … no. I'm sorry, Sebastian."

"What is it? Are you hurt?" He looks Kurt over, searching for any visible marks or bleeding, some sign of an injury.

"No, I'm not hurt," Kurt lies. "I … I was wrong. This … it wasn't what I wanted."

"Kurt …" Sebastian puts a hand on Kurt's shoulder, but Kurt recoils.

"P-please. Please, I … I need a minute to myself. I need to ..." Without finishing his thought, Kurt slides off the bed, avoiding Sebastian's touch as he collects his clothes and puts them back on – underwear, t-shirt, slacks, ticking them off in his head so he can keep his mind away from what happened. When he's mostly dressed, the rest he decides to carry with him. He'll go downstairs and call his dad to come get him. Then he'll wait outside and …

"Kurt?" Sebastian pulls on a pair of navy sweatpants and a white t-shirt in less time than it takes Kurt to reach the bedroom door. "Kurt, don't … please, don't leave."

"I'm sorry." Kurt grabs his blazer, worrying the fabric between his fingers, his eyes locked on the door. He's not itching to leave. Sebastian's room is as comforting to him as his own. But he can't stay. "But I can't … I can't be here right now."

"No!" Sebastian says. It's not commanding. It's disbelieving. Devastated. "I-I did what you asked me to, Kurt! You said this wouldn't ruin our friendship! You … I …" Sebastian goes dumb, mouth hanging open, shaking his head. This is the exact opposite of everything Kurt said would happen! The exact opposite of everything Sebastian wanted! "Y-you're the best friend I have, Kurt! Kurt, please, don't leave! Not like this. I … I can't lose you, Kurt! I can't …!"

Sebastian chokes on the end of his sentence, and Kurt turns around. He looks at his friend – desperate, frantic, heartbroken. Kurt's head tugs him towards the door, but his heart is leading him back. Kurt has always been the kind of person to follow his head before his heart, no matter how painful that's been for him in the past.

But not this time. Not when something more important than both is on the line.

Kurt wasn't alone in this. He didn't spend the past hour fucking himself. There was someone else, a reluctant participant whose feelings Kurt hadn't considered as much as he should have.

A boy who Kurt loves, who made his first time magical.

A boy who Kurt will have used if he walks out the door.

Sebastian may have started out the bully when the two of them met back in middle school, but it's Kurt who turned out to be the jerk.

He puts his things down.

"You're right." Kurt sniffles. "You're absolutely right, and I'm sorry." He walks over to his friend and wraps his arms around his waist. "Please … hold me?"

Sebastian's arms move in slow motion, winding around Kurt's body, hurt feelings making him insecure. But as soon as his hands feel the warmth of Kurt's body, he holds him tight, rocking Kurt in his arms. It feels nice to hold him like this.

It feels damn near close to perfect.

Sebastian wants this for as long as he can have it, but he doesn't know how to make that happen.

Not when he narrowly stopped Kurt from bolting out the door.

"What do we do now?" Kurt asks.

"I don't know," Sebastian says. "But please, tell me you'll stay so we can work this out? Please?"

"I will," Kurt says. Those two words work their way into Sebastian's soul and he holds Kurt tighter. "I promise."


	2. Red Light Green Light

**After Kurt's first time with his best friend, Sebastian, the two boys realize that there is too much unsaid between them to leave things the way they are. But will talking about it bring them together ... or push them apart?**

 _Sebastian's fingers trail slowly up Kurt's sides, slipping underneath his t-shirt to slide the fabric up his body. Kurt does the same to Sebastian's shirt, but with fingers that tremble as they go, unintentionally spreading goosebumps along Sebastian's skin. When Kurt's fingers reach the spot just below Sebastian's armpits where his ribs curl towards his pecs, his elbows clamp down tight to his sides._

 _"Op! I forgot you're ticklish!" Kurt says, juggling a giggle and a gasp as Sebastian retaliates by lightly licking his neck. Kurt squirms to get away, but Sebastian puts a hand to his cheek and holds him in place._

 _"Yeah" - Sebastian grins, sucking on the one spot he knows will make Kurt squeal like a piglet - "but I didn't …"_

* * *

"What was your first time like?"

Sebastian inhales deeply, then sighs into the air above him. This isn't the conversation he was hoping they'd be having when they finished hugging and returned to Sebastian's bed. He's not in the mood to talk about this, though he can see how the current atmosphere might have lead them in this direction. He'd wanted to talk about it when it happened, and definitely with Kurt, but Kurt made it clear that he wasn't comfortable with the subject, and Sebastian let it drop. He figured he'd shoot the shit with one of his other friends another time. But when it came up one afternoon after lacrosse practice, strangely enough, it seemed too personal. As much as Sebastian couldn't care less about locker room talk when other guys did it, he didn't want to participate. It seemed tacky and immature.

This isn't going to be locker room talk, but it's a sore spot for the both of them.

At least they're talking here and not over the phone.

At least Kurt stayed.

"I thought you didn't want to hear about it," Sebastian says in a wry rendition of his best friend's voice. "I thought you _never_ wanted to hear about it."

"Yeah, well, I've come to the conclusion that that might have been a jerk move on my part." Kurt rolls his head to the side to look at Sebastian, eyes full of regret. "You're my best friend. That was a big step in your life, I assume. You should be able to talk to me about it."

Sebastian tightens his grip on Kurt's hand, partially for security, and partially so Kurt doesn't let go when he hears the answer. They're about to enter touchy territory, even if it is ancient history as far as Sebastian is concerned.

"It was okay, I guess." He shrugs, then turns his head to meet Kurt's gaze. The two stare at one another in silent challenge - Sebastian praying Kurt will change the subject, Kurt waiting patiently for more. Sebastian blinks first. He sighs again. Here he is, stuck in another situation he sees no way out of. But if there was ever a time for him to bear his soul, now is that time. If he had told Kurt originally how his reluctance to let Sebastian confide in him had hurt him, they might not be in this position, good or bad. "Honestly, it was pretty awful."

"How?"

"Well, neither of us knew what we were doing. We screwed up trying to open the lube and made a huge mess. He scratched my thigh with his toe nail, and it really hurt. Somebody farted …" Sebastian pinches his lower lip between his teeth and his cheeks turn red, giving Kurt the impression that _he_ may have been that person.

"Was he someone from our school?"

"Nah. He was some guy I met at _Scandals_." Sebastian looks sheepishly down at the comforter beneath them, eyes tracing a line of stitching close to his face. "He said he was twenty-one, but I don't think he was. He seemed younger … our age. Anyway, he doesn't go to school with us. I've never seen him again."

Kurt has to admit he's relieved. He had thought all of Sebastian's sex partners were boys from Dalton. Seeing their faces every day, how they watched Sebastian in the hallway with wide, puppy-dog eyes, forever hoping he'd glance their way, stung. Kurt didn't know how he would handle finding out which one of those constantly pleading boys was Sebastian's first.

Knowing that none of them were is a huge weight off Kurt's shoulders.

Casual sex is one thing, and yes, virginity is a stupid societal construct that shouldn't amount for anything, so technically your first sexual experience shouldn't hold any more weight than your last.

Call him a sentimental fool but, to Kurt, in some ways it does.

In retrospect, the reason why Sebastian never did look their way was usually because he and Kurt were together, and Sebastian was looking at him.

* * *

 _Sebastian kisses Kurt tenderly, urgently, possessively, passionately, each one translating want and longing and desire in ways words could never properly express. And between each kiss, he gazes into Kurt's eyes, brow pulled in the center as if he can't believe that Kurt is there. But he is there, and they're together, making love on Sebastian's bed the way Sebastian had dreamed of so many times. All he has to do is reach out and touch him - Kurt's soft skin beneath Sebastian's fingertips proof of his existence in this fantasy come to life. Now that he has Kurt, there are no others. His past is just that – the past. And it's gone, erased completely every time Kurt kisses him back, looks him in the eyes, and smiles – blissful, bashful, and beautiful._

* * *

"Were you guys safe?" Kurt asks, digging deeper for his own peace of mind. Maybe Kurt should be a bit more sensitive considering they're talking about the boy/man Sebastian lost his virginity to, but someone he met at _Scandals_? Kurt can't imagine Sebastian, of all people, being so careless.

Sebastian may be daring, but he's not reckless.

"Of course, we were," Sebastian admits with some embarrassment. He knew that Kurt would scold him over this if he ever found it, but he was confident Kurt never would. Besides, he'd shouldered that responsibility, berating himself plenty for losing his virginity to some rando in a bar. "I swear. I made sure I took condoms with me when I went," Sebastian defends himself quickly, but his voice peters off when he realizes how bad that sounds, how it cements the fact that he'd gone to _Scandals_ on the lookout for a fuck "… you know … just in case ..."

Kurt stops himself before he can huff or make some other judgmental noise. Kurt started this. He's clearing the air. It's important to him. He doesn't want there to be secrets between them. But honestly, Sebastian isn't required to answer him if he doesn't want to. Kurt should be grateful that Sebastian is willing to give him a second chance at being the friend he should have been when this happened.

"So, it sounds like you were on a mission," Kurt teases to break the tension.

"Yeah." Sebastian chuckles tensely. "I guess … I guess I was."

"Mission accomplished?"

"No," Sebastian says, and it's true. It was true then, and it's doubly true now. "If I could take it back and replace it with what we just did, I would in a heartbeat."

* * *

 _"Whoa … no-no-no … oh … whoops!"_

 _Sebastian over-enthusiastically rips open the condom wrapper, fumbles the lubricated disk, and sends it flying across the room. Both boys watch it, snickering as it disappears in a corner behind Sebastian's desk. Kurt falls back on the pillows and snorts while Sebastian, laughing just as hard, struggles to catch his breath._

 _"Well, that's never happened before."_

 _"There's a first time for everything." Kurt reaches for Sebastian's stash of condoms that he keeps under his pillows. Kurt had raised an eyebrow at that when he saw Sebastian fish one out, and the sheepish expression returned to Sebastian's face._

 _"Uh … I keep them under there just in case," Sebastian had said, darting his eyes, unable to decide on a spot for them to settle._

 _"Who were you expecting?"_

 _"No one! I swear! It's been a few months and I … kind of forgot they were there."_

 _"Ugh!" Kurt groaned._

 _"What?"_

 _"How long has it been since you changed these sheets!?"_

 _Sebastian didn't answer, but the conversation at large had been swept under the proverbial carpet when Sebastian began rutting against Kurt, convincing him with long sweeps of his tongue over the sensitive skin at the juncture of his neck to forget about it._

 _And Kurt, melting into a potentially filthy comforter, did._

 _Sebastian goes to take the condom from him, but Kurt palms it._

 _"Can I?" Kurt asks, gesturing towards Sebastian cock. "Do you mind if I try …?"_

 _"No," Sebastian says, gulping so hard he's sure he's shoved his heart down a foot. "Not at all. G-give it a try." He kneels up, straddling Kurt's hips to give him space to work. He watches Kurt pinch the tip the way their teacher showed them in health class, place it gently over the head of Sebastian's cock, and roll it down with excruciating slowness. He rolls it to the base of Sebastian's cock, then runs a hand over it to remove any air bubbles._

 _"There," Kurt says, looking up at Sebastian for approval. "Is that … is that okay?"_

 _"Okay?" Sebastian winds his arms around Kurt's torso, squeezing him so hard he cracks his spine. "It's more than okay! I think that's the hottest thing I've ever fucking seen!"_

* * *

"Wh-why did you do it?"

This is the question. _The_ question. Sebastian can tell by the sound of Kurt's voice when he asks it. This is the one he's been waiting to ask, the one he's probably been dreading. The one that had festered in the back of his mind every time Kurt saw Sebastian a morning after. It was on those mornings that Sebastian should have realized how much he was hurting Kurt. But sex doesn't equal love … or maturity, and when it came to Kurt and his feelings, Sebastian had a tendency to be a little bit naïve.

He'd thought that, when it came to pining over Kurt, the only person he was hurting was himself.

"I was curious. Wanted to see what all the fuss was about. And, kind of like you, I wanted to get it over with."

Kurt's hand goes rigid in Sebastian's grasp and he can't understand why until he remembers what Kurt said to him in his car on the way over:

 _"I think … I kind of always knew that my first time would be with you anyway …"_

What if that wasn't resignation? What if Kurt had been waiting for him? Subconsciously saving himself for him? Kurt said that other boys don't want him, but what if that isn't entirely the truth? What if Kurt can't see the ones who do because he wanted Sebastian first?

Sebastian had wanted Kurt, too. He just didn't wait for him.

* * *

 _"Now, are you sure about this?"_

 _"Are we going to go through this again?" Kurt asks with a smirk. "Because it was exhausting the first time."_

 _"Yes," Sebastian pouts. "I don't want to hurt you. I mean, you just did it for the first time about fifteen minutes ago. You have to be sore."_

 _"Maybe a little," Kurt says, making a face when he shifts to the side and a throb in his ass confirms that yes, he is sore. "But not too much. Just … go slow."_

 _"You know, we don't have to have sex the way we did before." Sebastian bends low to Kurt's ear, whispering in that dark, seductive voice that was so startling to Kurt when he first heard it, but which sends all sorts of delicious chills up his spine. "I can suck you off. It'll be just as good. I promise."_

 _Kurt bites his lower lip, tempted by the offer, but confused by the ball of hot and hurt that statement puts in his stomach. He shakes his head. It's an answer, but it's also an attempt to brush that ball aside._

 _"Maybe some other time? I really, really want this. Unless you … you don't …"_

 _Sebastian rushes forward and collects the end of that sentence in a kiss. "Kurt, there won't ever be a day when I don't want to make love to you."_

* * *

"Were any other times awful?" Kurt asks while Sebastian wrestles with his conscience.

"A lot of the times were. It's just an act when you don't feel anything for the person you're with." He raises Kurt's hand to his mouth and kisses it. "It's better with feelings."

Kurt licks his dry lips, chewing around a smile. "Then, why did you keep doing it?"

"Because, physically, it felt good. It's great for stress relief. And besides, once you have sex, you kind of feel pressure to keep having it, whether you want to or not."

"Was there ever anyone you were with that you _liked_? I mean, that you wanted to be boyfriends with?"

Regardless of what Sebastian believes, this is actually _the_ question. The one that fills Kurt with fear. Sebastian may have had sex with a lot of boys at Dalton, but he's far from indiscriminate. Kurt knows the boys he slept with numbered amongst the more handsome, wealthier, upper GPA echelon of the student body. There was one boy in particular – Vail (named after the place his parents conceived him, apparently. What a story to tell the grandkids). He was an upperclassman, richer than Sebastian's family (if that's even possible without being actual royalty), smart, athletic, charming, and he drove a car that makes Kurt's Navigator look like the caboose on an old tyme toy train. To make matters worse, he wasn't a stuck-up prick. Then Kurt could hate him. He was a genuinely nice guy - a philanthropist, on the fast track to attending Harvard medical so he could someday travel the world and bring his medical expertise to impoverished nations.

If anyone was worthy of Sebastian, it was him.

As far as Kurt knows, Vail was the partner Sebastian was with off and on the longest. He loathed the day he'd find out the two of them had decided to make their undercover relationship official.

But Vail graduated last year, they hadn't heard from him since, and as far as Kurt could tell, Sebastian didn't seem to mourn the loss.

Of course, Sebastian is good at keeping his true feelings hidden, even from Kurt.

Kurt might be able to overlook the sex if Sebastian didn't like any of his partners enough to date them. God, that sounds awful, but some of the truest things in life do.

"No," Sebastian says in a tone that Kurt has no reason to doubt. "No one."

"Really?" Kurt asks, because even if he doesn't doubt him, he needs to make sure.

Sebastian smiles suddenly, looking at Kurt with a twinkle in his eyes. "Actually … uh … does today count?"

* * *

 _It's easier entering Kurt now that he's open, that he's comfortable with being touched. He knows Sebastian's fingers, knows what they're going to do. It's a touch he invites. It doesn't feel awkward or unnatural now that he knows what to expect. Sebastian uses twice as much lube as before. He knows that Kurt's sore, knows how sore he has to be, even if he's good at not showing it. If there's one thing Kurt has always been expert at hiding, it's pain. But now Sebastian can give Kurt the experience he'd wanted him to have._

 _He can look him in the eyes._

 _He can kiss him on the lips._

 _He can be face to face with him when he tells him he loves him._

* * *

"What makes me different?" Kurt asks, figuring he'll give Sebastian a break in the form of an easy question to answer. They're best friends, have been for close to a decade. They're comfortable with one another. They're compatible.

Isn't there a saying about dating your best friend?

"The difference is …" Sebastian runs a thumb over Kurt's knuckles. He has to keep touching him, has to keep reminding himself that what's happening is real, that with every question he answers, he gets closer and closer to something he's wanted for a long time "… I love you, Kurt."

"I love you, too."

"No. I mean … I love you. I love you more than anyone I've ever met. And the idea that you're going to find someone down the line and … and fall in love with them … make love to them …" Sebastian turns his face to the ceiling, fighting a well of angry tears "… maybe it makes me a hypocrite but, it kills me. Every time I picture it, I want to burn my eyes out. You know?"

Kurt could agree. He could admit he feels the same. He could lay on Sebastian's shoulders the depth of his despair since he began having sex. But he doesn't want to guilt his best friend. He's not about to shame him for his choices.

Sebastian has nothing to be ashamed of.

Besides, had Kurt been honest with Sebastian earlier, maybe things would be different now.

"Actually, I'm already in love with someone," Kurt confesses. Sebastian's face falls, but only for a second before Kurt squeezes his hand tighter, scoots a little closer. Sebastian's cheeks begin to burn. Kurt isn't used to seeing his best friend blush. He's beginning to enjoy that shade on him. "I have been for a while now. I just … I never had the courage to tell him."

"Do you think you might tell him soon?" Sebastian asks, moving with Kurt, curling in towards him and wrapping an arm around his waist.

"I think so," Kurt says. "Very, very soon."

* * *

 _"I love you, Sebastian. I … I love you. God!" There's a freedom in Kurt's voice, a brand new lack of shame when he says, "I'm cumming … oh God …"_

 _"I love you, too," Sebastian whimpers, speeding his hips to stay in sync with Kurt so they can cum together. To think, this entire time, they'd been on basically the same page and never knew it. Well, that stops today. As far as Sebastian is concerned, there isn't a single thought he has about their relationship that he will keep to himself again._

 _He pauses to move an inch closer, his pounding having slid him too far down the mattress, to discover that Kurt refuses to simply lay docile on the bed. He starts pushing back, meeting Sebastian's hips thrust for thrust, and that puts Sebastian over the edge._

* * *

"Do you _want_ to be my boyfriend?" Kurt asks. "We're going to college next year. Everything could change for us."

"It won't change that much. You're going to NYADA next year …"

"I am."

"… and I'm going to NYU …"

"Yup." Kurt smiles. He'd been frightened when he found out that he was going to his dream school in New York that this would be the end of his friendship with Sebastian - at least, the way it stood. Yes, they were best friends, and Kurt had faith in what they had. They had definitely fought hard enough for it. But distance can have one of two effects on a friendship – it makes the heart fonder, or more forgetful.

But then they found out that Sebastian had been accepted to _his_ dream school - NYU. Kurt felt that kismet had to be at play here somewhat. Nothing was going to get in the way of Kurt going after his dreams of performing on Broadway. Not even a broken heart. But Sebastian had been a part of his dreams for a long time now.

It was farfetched to believe he could have both.

But what if he could?

"So, if we started dating now, we could make this work," Sebastian says. Honestly, he'd been willing to try and make a long-distance relationship work if it came down to it, but this seems like an opportunity that they would be ridiculous not to take advantage of.

Sebastian doesn't believe in signs, but this seems like a pretty big one. He didn't have any doubts about getting into NYU. He had the grades, the extracurriculars, and there were plenty of spots available for incoming freshmen.

But for Kurt, NYADA only accepts a handful of graduating seniors per year. Being a student from Lima, Ohio, attending a school with very little in the way of arts in its curriculum, competing with kids from all over the country, some of whom have been groomed to attend NYADA since birth, the odds seemed stacked against him. Plus, Kurt didn't have a Plan B. Aside from NYADA, Kurt didn't have any other colleges lined up.

It was NYADA or nothing.

But Kurt wouldn't be Kurt if he didn't go up against impossible odds and emerge victorious.

"I'm willing to give it a try if you are," Kurt says.

"I am. And I want to, more than you'll ever know."

"Then can you do me a favor?" Kurt asks, his stomach quivering like the first time he ever performed on stage in front of a competition audience, but ready to jump into this relationship – the only one of his life so far – with both feet.

"What's that?"

Kurt puts a hand to Sebastian's cheek, pulling him closer, gaze flicking down to his lips, then back to his eyes. "Make love to me again?"


End file.
